US2016049597A1PendingUtilityA1
Organic electroluminescent materials and devices
Est. expiryAug 7, 2034(~8 yrs left)· nominal 20-yr term from priority
H01L 51/0085H01L 51/5012C07F 15/0033C09K 2211/185C09K 11/06H10K 50/11H10K 2101/10H10K 85/342
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Claims
Abstract
A compound having the formula Ir(L A ) n (L B ) 3-n is disclosed wherein L A is an aza-DBF ligand and L B is an alkyl-substituted phenylpyridine ligand, wherein the compound has a structure according to Formula I: wherein A 1 , A 2 , A 4 , A 5 , A 6 , A 7 , and A 8 comprise carbon or nitrogen; wherein at least one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen; wherein ring B is bonded to ring A through a C—C bond; wherein the iridium is bonded to ring A through a Ir—C bond; wherein X is O, S, or Sc; wherein R 1 and R 2 each independently represent mono-, di-, tri-, tetra-substitution, or no substitution; wherein R′ and R″ each independently represent mono-, di-substitution, or no substitution; wherein any adjacent substitutions in R′, R″, R 1 , R 3 , R 4 , R 5 , and R 6 are optionally linked together to form a ring; wherein R 1 , R 2 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof; wherein n is an integer from 1 to 3; and wherein total number of carbons in at least one of the pairs R 3 and R 4 , and R 5 and R 6 is at least four.
Claims
exact text as granted — not AI-modified1 . A compound having the formula Ir(L A ) n (L B ) 3-n , wherein L A is an aza-dibenzofuran ligand and L is an alkyl-substituted phenylpyridine ligand;
wherein the compound has a structure according to Formula I:
wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 comprise carbon or nitrogen;
wherein at least one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen;
wherein ring B is bonded to ring A through a C—C bond;
wherein the iridium is bonded to ring A through a Ir—C bond;
wherein X is O, S, or Se;
wherein R 1 and R 2 each independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
wherein R′ and R″ each independently represent mono-, di-substitution, or no substitution;
wherein any adjacent substitutions in R′, R″, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally linked together to form a ring;
wherein R 1 , R 2 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrite, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof;
wherein n is an integer from 1 to 3; and
wherein total number of carbons in at least one of the pairs R 3 and R 4 , and R 5 and R 6 is at least four.
2 . The compound of claim 1 , wherein n is 1.
3 . The compound of claim 1 , wherein the compound has a structure according to Formula II:
4 . The compound of claim 1 , wherein the compound has a structure according to Formula III:
5 . The compound of claim 1 , wherein the compound has a structure according to Formula IV:
6 . The compound of claim 1 , wherein only one of A 1 to A 8 is nitrogen.
7 . The compound of claim 6 , wherein one of A 5 to A 8 is nitrogen.
8 . The compound of claim 1 , wherein X is O.
9 . The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.
10 . The compound of claim 1 , wherein at least one of the following conditions (1) and (2) is true:
(1) R 3 and R 4 are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof; and total number carbons in R 3 and R 4 combined is at least four; and (2) R 5 and R 6 are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof; and total number of carbons in R 5 and R 6 combined is at least four.
11 . The compound of claim 1 , wherein at least one of the following conditions (1) and (2) is true:
(1) R 3 and R 4 are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof; at least one of R 3 and R 4 contain at least one deuterium; and total number of carbons in R 3 and R 4 combined is at least four; and (2) R 5 and R 6 are each independently selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, and combinations thereof; at least one of R 3 and R 4 contain at least one deuterium; and total number of carbons in R 5 and R 6 combined is at least four.
12 . The compound of claim 1 , wherein R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, and combinations thereof.
13 . The compound of claim 1 , wherein the compound has a structure according to Formula V:
wherein R is selected from the group consisting of alkyl, cycloalkyl, its partially or fully deuterated variants thereof, and combinations thereof.
14 . The compound of claim 13 , wherein R is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.
15 . The compound of claim 13 , wherein X is O.
16 . The compound of claim 1 , wherein L A is selected from the group consisting of:
17 . The compound of claim 1 , wherein L B is selected from the group consisting of
18 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
19 . A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode; a cathode; and an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound having a structure according to Formula I:
wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 comprise carbon or nitrogen;
wherein at least one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen;
wherein ring B is bonded to ring A through a C—C bond;
wherein the iridium is bonded to ring A through a Ir—C bond;
wherein X is O, S, or Se;
wherein R 1 and R 2 each independently represent mono-, di-, tetra-substitution, or no substitution;
wherein R′ and R″ each independently represent mono-, di-substitution, or no substitution;
wherein any adjacent substitutions in R′, R″, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally linked together to form a ring;
wherein R 1 , R 2 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrite, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof;
wherein n is an integer from 1 to 3; and
wherein total number of carbons in at least one of the pairs R 3 and R 4 , and R 5 and R 6 is at least four.
20 .- 29 . (canceled)
30 . A formulation comprising the compound having a structure according to Formula I:
wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , R 7 , and A 8 comprise carbon or nitrogen;
wherein at least one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen;
wherein ring B is bonded to ring A through a C—C bond;
wherein the iridium is bonded to ring A through a Ir—C bond;
wherein X is O, S, or Se;
wherein R 1 and R 2 each independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
wherein R′ and R″ each independently represent mono-, di-substitution, or no substitution;
wherein any adjacent substitutions in R′, R″, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally linked together to form a ring;
wherein R 1 , R 2 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof;
wherein n is an integer from 1 to 3; and
wherein total number of carbons in at least one of the pairs R 3 and R 4 , and R 5 and R 6 is at least four.Join the waitlist — get patent alerts
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